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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014679

Secondary Accession Numbers

HMDB14679

Metabolite Identification

Common Name

Toremifene

Description

Toremifene is only found in individuals that have used or taken this drug. It is a first generation nonsteroidal selective estrogen receptor modulator (SERM) that is structurally related to tamoxifen. Like tamoxifen, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue. [PubChem]Toremifene is a nonsteroidal triphenylethylene derivative. Toremifene binds to estrogen receptors and may exert estrogenic, antiestrogenic, or both activities, depending upon the duration of treatment, animal species, gender, target organ, or endpoint selected. The antitumor effect of toremifene in breast cancer is believed to be mainly due to its antiestrogenic effects, in other words, its ability to compete with estrogen for binding sites in the cancer, blocking the growth-stimulating effects of estrogen in the tumor. Toremifene may also inhibit tumor growth through other mechanisms, such as induction of apoptosis, regulation of oncogene expression, and growth factors.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

539
  Mrv0541 02231214452D          

 29 31  0  0  0  0            999 V2000
    3.0791    4.1251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
  2 21  1  0  0  0  0
  3 20  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 16  2  0  0  0  0
  8 17  1  0  0  0  0
  9 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 18 24  1  0  0  0  0
 19 25  2  0  0  0  0
 20 21  1  0  0  0  0
 22 26  2  0  0  0  0
 23 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0014679
     RDKit          3D
Toremifene
 57 59  0  0  0  0  0  0  0  0999 V2000
    6.2621   -1.7084   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.5871    0.6062 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6808   -0.3055    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -0.5433    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -0.2680    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -0.1994    1.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807    0.0563    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    0.1374    2.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.3893    1.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.5669    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1689    0.8338   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    0.1702   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    0.4658   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0346   -0.7800   -1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239   -0.4724   -2.2105 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -0.9363    0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519   -1.1404    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -2.2237    2.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576   -3.1432    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003   -2.9716    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317   -1.8729    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2183    1.8711   -1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.6847   -2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653    2.6726   -3.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    3.9217   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117    4.1269   -2.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    3.1234   -1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.4893   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5134    0.2373   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -2.6286    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -1.4870   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458   -1.8703   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6919   -0.3437    2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4794   -0.9385    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9433    0.7588    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5733    0.2613    2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -1.4830    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.7153    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8774   -1.0250    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    0.0026    3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.4485    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    0.6445    0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6101    1.2778   -1.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0955   -1.6515   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -1.1161   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -0.4372    2.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -2.3749    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7725   -4.0031    3.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -3.6947    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -1.8159   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680    0.6803   -3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583    2.4641   -4.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    4.6977   -4.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    5.1493   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    3.3844   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325    0.6173   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989    0.1732   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10 28  1  0
 28 29  2  0
 29  7  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

539
  Mrv0541 02231214452D          

 29 31  0  0  0  0            999 V2000
    3.0791    4.1251    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -4.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
  2 21  1  0  0  0  0
  3 20  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 16  2  0  0  0  0
  8 17  1  0  0  0  0
  9 18  2  0  0  0  0
  9 19  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 22  1  0  0  0  0
 17 23  2  0  0  0  0
 18 24  1  0  0  0  0
 19 25  2  0  0  0  0
 20 21  1  0  0  0  0
 22 26  2  0  0  0  0
 23 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014679

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-

> <INCHI_KEY>
XFCLJVABOIYOMF-QPLCGJKRSA-N

> <FORMULA>
C26H28ClNO

> <MOLECULAR_WEIGHT>
405.96

> <EXACT_MASS>
405.18594223

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
46.489635229995784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine

> <ALOGPS_LOGP>
5.65

> <JCHEM_LOGP>
6.269135194999999

> <ALOGPS_LOGS>
-6.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.764304427648634

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
133.41050000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
toremifene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014679
     RDKit          3D
Toremifene
 57 59  0  0  0  0  0  0  0  0999 V2000
    6.2621   -1.7084   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.5871    0.6062 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6808   -0.3055    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -0.5433    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -0.2680    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -0.1994    1.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807    0.0563    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    0.1374    2.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.3893    1.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.5669    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1689    0.8338   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    0.1702   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    0.4658   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0346   -0.7800   -1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239   -0.4724   -2.2105 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -0.9363    0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519   -1.1404    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -2.2237    2.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576   -3.1432    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003   -2.9716    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317   -1.8729    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2183    1.8711   -1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.6847   -2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653    2.6726   -3.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    3.9217   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117    4.1269   -2.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    3.1234   -1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.4893   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5134    0.2373   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -2.6286    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -1.4870   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458   -1.8703   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6919   -0.3437    2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4794   -0.9385    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9433    0.7588    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5733    0.2613    2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -1.4830    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.7153    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8774   -1.0250    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    0.0026    3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.4485    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    0.6445    0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6101    1.2778   -1.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0955   -1.6515   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -1.1161   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -0.4372    2.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -2.3749    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7725   -4.0031    3.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -3.6947    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -1.8159   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680    0.6803   -3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583    2.4641   -4.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    4.6977   -4.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    5.1493   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    3.3844   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325    0.6173   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989    0.1732   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10 28  1  0
 28 29  2  0
 29  7  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 539                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       5.748   7.700   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.415  -3.080   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -6.160   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.081  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.416   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.416   5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.748  -7.700   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   13   21                                                       
CONECT    3   20   28   29                                                  
CONECT    4    5    6    8                                                  
CONECT    5    4    7    9                                                  
CONECT    6    4   10   11                                                  
CONECT    7    5   12                                                       
CONECT    8    4   16   17                                                  
CONECT    9    5   18   19                                                  
CONECT   10    6   14                                                       
CONECT   11    6   15                                                       
CONECT   12    1    7                                                       
CONECT   13    2   14   15                                                  
CONECT   14   10   13                                                       
CONECT   15   11   13                                                       
CONECT   16    8   22                                                       
CONECT   17    8   23                                                       
CONECT   18    9   24                                                       
CONECT   19    9   25                                                       
CONECT   20    3   21                                                       
CONECT   21    2   20                                                       
CONECT   22   16   26                                                       
CONECT   23   17   26                                                       
CONECT   24   18   27                                                       
CONECT   25   19   27                                                       
CONECT   26   22   23                                                       
CONECT   27   24   25                                                       
CONECT   28    3                                                            
CONECT   29    3                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0014679
HETATM    1  C1  UNL     1       6.262  -1.708  -0.273  1.00  0.00           C  
HETATM    2  N1  UNL     1       6.367  -0.587   0.606  1.00  0.00           N  
HETATM    3  C2  UNL     1       7.681  -0.306   1.092  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.335  -0.543   1.620  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.030  -0.268   0.939  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.932  -0.199   1.817  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.681   0.056   1.252  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.550   0.137   2.055  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.699   0.389   1.525  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.855   0.567   0.178  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.169   0.834  -0.426  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.223   0.170  -0.105  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.551   0.466  -0.722  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.035  -0.780  -1.443  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -6.624  -0.472  -2.211  1.00  0.00          CL  
HETATM   16  C13 UNL     1      -3.115  -0.936   0.844  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.952  -1.140   1.913  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.838  -2.224   2.761  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.858  -3.143   2.544  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.000  -2.972   1.482  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.132  -1.873   0.639  1.00  0.00           C  
HETATM   22  C19 UNL     1      -2.218   1.871  -1.465  1.00  0.00           C  
HETATM   23  C20 UNL     1      -2.705   1.685  -2.737  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.765   2.673  -3.696  1.00  0.00           C  
HETATM   25  C22 UNL     1      -2.305   3.922  -3.351  1.00  0.00           C  
HETATM   26  C23 UNL     1      -1.812   4.127  -2.079  1.00  0.00           C  
HETATM   27  C24 UNL     1      -1.763   3.123  -1.136  1.00  0.00           C  
HETATM   28  C25 UNL     1       0.254   0.489  -0.625  1.00  0.00           C  
HETATM   29  C26 UNL     1       1.513   0.237  -0.105  1.00  0.00           C  
HETATM   30  H1  UNL     1       5.970  -2.629   0.255  1.00  0.00           H  
HETATM   31  H2  UNL     1       5.475  -1.487  -1.048  1.00  0.00           H  
HETATM   32  H3  UNL     1       7.246  -1.870  -0.771  1.00  0.00           H  
HETATM   33  H4  UNL     1       7.692  -0.344   2.208  1.00  0.00           H  
HETATM   34  H5  UNL     1       8.479  -0.939   0.650  1.00  0.00           H  
HETATM   35  H6  UNL     1       7.943   0.759   0.819  1.00  0.00           H  
HETATM   36  H7  UNL     1       5.573   0.261   2.343  1.00  0.00           H  
HETATM   37  H8  UNL     1       5.291  -1.483   2.209  1.00  0.00           H  
HETATM   38  H9  UNL     1       4.115   0.715   0.412  1.00  0.00           H  
HETATM   39  H10 UNL     1       3.877  -1.025   0.131  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.631   0.003   3.121  1.00  0.00           H  
HETATM   41  H12 UNL     1      -1.558   0.449   2.219  1.00  0.00           H  
HETATM   42  H13 UNL     1      -5.254   0.645   0.158  1.00  0.00           H  
HETATM   43  H14 UNL     1      -4.610   1.278  -1.401  1.00  0.00           H  
HETATM   44  H15 UNL     1      -5.096  -1.651  -0.752  1.00  0.00           H  
HETATM   45  H16 UNL     1      -4.363  -1.116  -2.251  1.00  0.00           H  
HETATM   46  H17 UNL     1      -4.739  -0.437   2.118  1.00  0.00           H  
HETATM   47  H18 UNL     1      -4.506  -2.375   3.603  1.00  0.00           H  
HETATM   48  H19 UNL     1      -2.773  -4.003   3.223  1.00  0.00           H  
HETATM   49  H20 UNL     1      -1.208  -3.695   1.288  1.00  0.00           H  
HETATM   50  H21 UNL     1      -1.411  -1.816  -0.186  1.00  0.00           H  
HETATM   51  H22 UNL     1      -3.068   0.680  -3.048  1.00  0.00           H  
HETATM   52  H23 UNL     1      -3.158   2.464  -4.675  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.350   4.698  -4.098  1.00  0.00           H  
HETATM   54  H25 UNL     1      -1.462   5.149  -1.875  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.356   3.384  -0.158  1.00  0.00           H  
HETATM   56  H27 UNL     1       0.233   0.617  -1.711  1.00  0.00           H  
HETATM   57  H28 UNL     1       2.399   0.173  -0.724  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4
CONECT    3   33   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7
CONECT    7    8    8   29
CONECT    8    9   40
CONECT    9   10   10   41
CONECT   10   11   28
CONECT   11   12   12   22
CONECT   12   13   16
CONECT   13   14   42   43
CONECT   14   15   44   45
CONECT   16   17   17   21
CONECT   17   18   46
CONECT   18   19   19   47
CONECT   19   20   48
CONECT   20   21   21   49
CONECT   21   50
CONECT   22   23   23   27
CONECT   23   24   51
CONECT   24   25   25   52
CONECT   25   26   53
CONECT   26   27   27   54
CONECT   27   55
CONECT   28   29   29   56
CONECT   29   57
END

HMDB0014679
     RDKit          3D
Toremifene
 57 59  0  0  0  0  0  0  0  0999 V2000
    6.2621   -1.7084   -0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3671   -0.5871    0.6062 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6808   -0.3055    1.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -0.5433    1.6197 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -0.2680    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9318   -0.1994    1.8170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6807    0.0563    1.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    0.1374    2.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986    0.3893    1.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548    0.5669    0.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1689    0.8338   -0.4262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2234    0.1702   -0.1047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    0.4658   -0.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0346   -0.7800   -1.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6239   -0.4724   -2.2105 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1152   -0.9363    0.8444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519   -1.1404    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8381   -2.2237    2.7605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576   -3.1432    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003   -2.9716    1.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317   -1.8729    0.6390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2183    1.8711   -1.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.6847   -2.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7653    2.6726   -3.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    3.9217   -3.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117    4.1269   -2.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7627    3.1234   -1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542    0.4893   -0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5134    0.2373   -0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -2.6286    0.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -1.4870   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2458   -1.8703   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6919   -0.3437    2.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4794   -0.9385    0.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9433    0.7588    0.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5733    0.2613    2.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -1.4830    2.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.7153    0.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8774   -1.0250    0.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    0.0026    3.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5580    0.4485    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2544    0.6445    0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6101    1.2778   -1.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0955   -1.6515   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3632   -1.1161   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394   -0.4372    2.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5056   -2.3749    3.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7725   -4.0031    3.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075   -3.6947    1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -1.8159   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680    0.6803   -3.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1583    2.4641   -4.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3503    4.6977   -4.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616    5.1493   -1.8749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3556    3.3844   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2325    0.6173   -1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989    0.1732   -0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 10 28  1  0
 28 29  2  0
 29  7  1  0
 21 16  1  0
 27 22  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  8 40  1  0
  9 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
 26 54  1  0
 27 55  1  0
 28 56  1  0
 29 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Toremifeno	ChEBI
Toremifenum	ChEBI
Fareston	Kegg
Toremifene citrate (1:1)	HMDB
Toremifene, (e)-isomer	HMDB
Citrate, toremifene	HMDB
Toremifene citrate	HMDB

Chemical Formula

C₂₆H₂₈ClNO

Average Molecular Weight

405.96

Monoisotopic Molecular Weight

405.18594223

IUPAC Name

(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine

Traditional Name

toremifene

CAS Registry Number

89778-26-7

SMILES

CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-

InChI Key

XFCLJVABOIYOMF-QPLCGJKRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Diphenylmethane
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alkyl halide
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:9635 )
tertiary amine (CHEBI:9635 )
organochlorine compound (CHEBI:9635 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014679)
Membrane (HMDB: HMDB0014679)

Source

Exogenous

Exogenous (HMDB: HMDB0014679)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	108 - 110 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00041 g/L	Not Available
LogP	6.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
logP	5.65	ALOGPS
logP	6.27	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.41 m³·mol⁻¹	ChemAxon
Polarizability	46.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	199.668	30932474
DeepCCS	[M-H]-	197.245	30932474
DeepCCS	[M-2H]-	231.601	30932474
DeepCCS	[M+Na]+	207.187	30932474
AllCCS	[M+H]+	200.3	32859911
AllCCS	[M+H-H2O]+	197.7	32859911
AllCCS	[M+NH4]+	202.8	32859911
AllCCS	[M+Na]+	203.5	32859911
AllCCS	[M-H]-	196.2	32859911
AllCCS	[M+Na-2H]-	195.8	32859911
AllCCS	[M+HCOO]-	195.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.41 minutes	32390414
Predicted by Siyang on May 30, 2022	15.4849 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2650.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	326.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	706.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	765.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	151.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1617.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	595.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1624.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	478.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	217.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	147.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Toremifene	CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1	4199.0	Standard polar	33892256
Toremifene	CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1	3000.6	Standard non polar	33892256
Toremifene	CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1	2991.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Toremifene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9123000000-e8ca7915f080abef6c64	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Toremifene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Toremifene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Toremifene , positive-QTOF	splash10-0a4i-0010900000-f55f03796d8b627e24e1	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 10V, Positive-QTOF	splash10-0a4i-2336900000-2e971ee90e59a5120d04	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 20V, Positive-QTOF	splash10-00di-9335100000-10319dabbd76e118d141	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 40V, Positive-QTOF	splash10-00di-6191000000-b6988a63b5bdf3bd0d81	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 10V, Negative-QTOF	splash10-0udi-1004900000-25e7558863d6df07b3f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 20V, Negative-QTOF	splash10-0f89-1039300000-a248ed46fb935057a8cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 40V, Negative-QTOF	splash10-001j-4196000000-03eaf6c4478f21e63114	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 10V, Negative-QTOF	splash10-0udi-0001900000-b620000c77b943ad556b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 20V, Negative-QTOF	splash10-001i-9001000000-70de6f1304f8eda50aab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 40V, Negative-QTOF	splash10-0002-0093000000-712ff7353d5c4103cead	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 10V, Positive-QTOF	splash10-0a4i-0000900000-45f3f39668f0f5230f47	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 20V, Positive-QTOF	splash10-0pi0-6077900000-511599e4ed6373eddd32	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Toremifene 40V, Positive-QTOF	splash10-00di-9220000000-a931f703a5617577d812	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00539	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00539	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00539

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2275722

KEGG Compound ID

C08166

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Toremifene

METLIN ID

Not Available

PubChem Compound

3005573

PDB ID

Not Available

ChEBI ID

9635

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ariazi EA, Ariazi JL, Cordera F, Jordan VC: Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. [PubMed:16515478 ]
Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
Price N, Sartor O, Hutson T, Mariani S: Role of 5a-reductase inhibitors and selective estrogen receptor modulators as potential chemopreventive agents for prostate cancer. Clin Prostate Cancer. 2005 Mar;3(4):211-4. [PubMed:15882476 ]
Musa MA, Khan MO, Cooperwood JS: Medicinal chemistry and emerging strategies applied to the development of selective estrogen receptor modulators (SERMs). Curr Med Chem. 2007;14(11):1249-61. [PubMed:17504144 ]
Thompson IM: Chemoprevention of prostate cancer: agents and study designs. J Urol. 2007 Sep;178(3 Pt 2):S9-S13. Epub 2007 Jul 20. [PubMed:17644117 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
Kivisto KT, Villikka K, Nyman L, Anttila M, Neuvonen PJ: Tamoxifen and toremifene concentrations in plasma are greatly decreased by rifampin. Clin Pharmacol Ther. 1998 Dec;64(6):648-54. [PubMed:9871429 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Locci P, Bellocchio S, Lilli C, Marinucci L, Cagini L, Baroni T, Giustozzi G, Balducci C, Becchetti E: Synthesis and secretion of transforming growth factor-beta1 by human desmoid fibroblast cell line and its modulation by toremifene. J Interferon Cytokine Res. 2001 Nov;21(11):961-70. [PubMed:11747628 ]
Liu X, Pisha E, Tonetti DA, Yao D, Li Y, Yao J, Burdette JE, Bolton JL: Antiestrogenic and DNA damaging effects induced by tamoxifen and toremifene metabolites. Chem Res Toxicol. 2003 Jul;16(7):832-7. [PubMed:12870885 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Jones KL, Buzdar AU: A review of adjuvant hormonal therapy in breast cancer. Endocr Relat Cancer. 2004 Sep;11(3):391-406. [PubMed:15369444 ]
Shelly W, Draper MW, Krishnan V, Wong M, Jaffe RB: Selective estrogen receptor modulators: an update on recent clinical findings. Obstet Gynecol Surv. 2008 Mar;63(3):163-81. doi: 10.1097/OGX.0b013e31816400d7. [PubMed:18279543 ]
Gennari L, Merlotti D, Valleggi F, Martini G, Nuti R: Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. Drugs Aging. 2007;24(5):361-79. [PubMed:17503894 ]
Lewis-Wambi JS, Jordan VC: Treatment of Postmenopausal Breast Cancer with Selective Estrogen Receptor Modulators (SERMs). Breast Dis. 2005-2006;24:93-105. [PubMed:16917142 ]
Ariazi EA, Ariazi JL, Cordera F, Jordan VC: Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. [PubMed:16515478 ]
Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
Goldstein LJ: Controversies in adjuvant endocrine treatment of premenopausal women. Clin Breast Cancer. 2006 Feb;6 Suppl 2:S36-40. [PubMed:16595024 ]
Smith MR: Treatment-related osteoporosis in men with prostate cancer. Clin Cancer Res. 2006 Oct 15;12(20 Pt 2):6315s-6319s. [PubMed:17062721 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]

Showing metabocard for Toremifene (HMDB0014679)

MOL for HMDB0014679 (Toremifene)

3D MOL for HMDB0014679 (Toremifene)

3D SDF for HMDB0014679 (Toremifene)

3D-SDF for HMDB0014679 (Toremifene)

PDB for HMDB0014679 (Toremifene)

3D PDB for HMDB0014679 (Toremifene)

SMILES for HMDB0014679 (Toremifene)

INCHI for HMDB0014679 (Toremifene)

Structure for HMDB0014679 (Toremifene)

3D Structure for HMDB0014679 (Toremifene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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References

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Transporters

References